DE837098C - Process for the preparation of quaternary 3-oxyphenylammonium compounds - Google Patents
Process for the preparation of quaternary 3-oxyphenylammonium compoundsInfo
- Publication number
- DE837098C DE837098C DEH7251A DEH0007251A DE837098C DE 837098 C DE837098 C DE 837098C DE H7251 A DEH7251 A DE H7251A DE H0007251 A DEH0007251 A DE H0007251A DE 837098 C DE837098 C DE 837098C
- Authority
- DE
- Germany
- Prior art keywords
- oxyphenyl
- compound
- compounds
- solution
- anion
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 150000001450 anions Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WAVOOWVINKGEHS-UHFFFAOYSA-N 3-(diethylamino)phenol Chemical compound CCN(CC)C1=CC=CC(O)=C1 WAVOOWVINKGEHS-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- CDAWCLOXVUBKRW-UHFFFAOYSA-N 2-aminophenol Chemical class NC1=CC=CC=C1O CDAWCLOXVUBKRW-UHFFFAOYSA-N 0.000 claims description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- MESJRHHDBDCQTH-UHFFFAOYSA-N 3-(dimethylamino)phenol Chemical compound CN(C)C1=CC=CC(O)=C1 MESJRHHDBDCQTH-UHFFFAOYSA-N 0.000 description 4
- NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- -1 ethyl halide Chemical class 0.000 description 3
- XFKDMVZXPKLBQS-UHFFFAOYSA-N ethyl(dimethyl)azanium;iodide Chemical compound [I-].CC[NH+](C)C XFKDMVZXPKLBQS-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 2
- DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 2
- 229940008406 diethyl sulfate Drugs 0.000 description 2
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 2
- INFSYNLQBZDWRI-UHFFFAOYSA-N n-ethyl-n-methylethanamine;hydrobromide Chemical compound [Br-].CC[NH+](C)CC INFSYNLQBZDWRI-UHFFFAOYSA-N 0.000 description 2
- 229910001923 silver oxide Inorganic materials 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- AOQFXDJMDVIWBZ-UHFFFAOYSA-N diethyl(methyl)azanium methyl sulfate Chemical compound CC[NH+](C)CC.COS([O-])(=O)=O AOQFXDJMDVIWBZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- RHZNQEWFWUODFC-UHFFFAOYSA-N ethyl(dimethyl)azanium;ethyl sulfate Chemical compound CC[NH+](C)C.CCOS([O-])(=O)=O RHZNQEWFWUODFC-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CQWWONKCVFKXRE-UHFFFAOYSA-N n,n-dimethylethanamine;hydrobromide Chemical compound [Br-].CC[NH+](C)C CQWWONKCVFKXRE-UHFFFAOYSA-N 0.000 description 1
- KSKTVNNRMXUMIY-UHFFFAOYSA-N n,n-dimethylethanamine;hydrochloride Chemical compound Cl.CCN(C)C KSKTVNNRMXUMIY-UHFFFAOYSA-N 0.000 description 1
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 1
- GNVRJGIVDSQCOP-UHFFFAOYSA-N n-ethyl-n-methylethanamine Chemical class CCN(C)CC GNVRJGIVDSQCOP-UHFFFAOYSA-N 0.000 description 1
- LDELZSZVJXFFIE-UHFFFAOYSA-N n-ethyl-n-methylethanamine;4-methylbenzenesulfonic acid Chemical compound CCN(C)CC.CC1=CC=C(S(O)(=O)=O)C=C1 LDELZSZVJXFFIE-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C215/00—Compounds containing amino and hydroxy groups bound to the same carbon skeleton
- C07C215/74—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C215/90—Compounds containing amino and hydroxy groups bound to the same carbon skeleton having hydroxy groups and amino groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with quaternised amino groups bound to the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von quaternären 3-Oxyphenylammoniumverbindungen Die Erfindung betrifft die Herstellung von (3-Oxyphenyl)-äthyldimethylammonium-und (3-Oxyphenyl)-diäthylmethylammoniumverbindungen, insbesondere solcher der folgenden allgemeinen Formel in welcher R eine Methyl- oder Äthylgruppe, und X ein Anion, beispielsweise Chlor, Brom, Jod, p-Toluolsulfonyloxy (p-CH,C@H,S03 ), Methylsulfat (CH,S04 ), Äthylsulfat (C,H,S04) und andere ähnliche Ionen, bedeuten. Diese neuen Verbindungen sind infolge ihrer die Wirkung von Curare aufhebenden Eigenschaften wertvoll.Process for the preparation of quaternary 3-oxyphenylammonium compounds The invention relates to the preparation of (3-oxyphenyl) ethyldimethylammonium and (3-oxyphenyl) diethylmethylammonium compounds, in particular those of the following general formula in which R is a methyl or ethyl group and X is an anion, for example chlorine, bromine, iodine, p-toluenesulfonyloxy (p-CH, C @ H, S03), methyl sulfate (CH, S04), ethyl sulfate (C, H, S04 ) and other similar ions. These new compounds are valuable because of their curare-canceling properties.
Es wurde nun gefunden, daß die Verbindungen der obigen Formel dadurch hergestellt werden können, daß ein substituiertes Aminophenol der Formel mittels einer Verbindung der Formel H (C Hz)," - X, (I I I) quaternisiert wird; in diesen Formeln hat X die gleiche Bedeutung wie oben und k, m und n stehen für die Zahlen i oder 2, wobei die Summe von k+m+n stets 4 oder 5 beträgt.It has now been found that the compounds of the above formula can be prepared in that a substituted aminophenol of the formula is quaternized by means of a compound of the formula H (C Hz), "- X, (III); in these formulas, X has the same meaning as above and k, m and n stand for the numbers i or 2, where the sum of k + m + n is always 4 or 5.
Die Verbindungen der Formel (I), worin R eine Methylgruppe bedeutet, werden vorzugsweise dadurch erhalten, daß m-Dimethylaminophenol mittels einer Verbindung quaternisiert wird, welche zur Einführung der Äthylgruppe und eines Anions befähigt ist, wie z. B. ein Äthylhalogenid, Diäthylsulfat, oder p-Toluolsulfosäureäthylester; diejenigen Verbindungen, in deren Formel R eine Äthylgruppe bedeutet, werden am besten dadurch erhalten, daß m-Diäthylaminophenol mittels einer Verbindung quaternisiert wird, welche zur Einführung einer Methylgruppe und eines Anions befähigt ist, wie beispielsweise ein Methylhalogenid, Dimethylsulfat oder p-Toluolsulfosäuremethylester. Von den nach dem erfindungsgemäßen Verfahren erhältlichen Verbindungen sind diejenigen nach Formel (I), worin X ein Halogen, beispielsweise Chlor, Brom oder Jod darstellt, am wertvollsten, da sie leicht in kristallisierter Form gebildet werden. Beispiel i (3-Oxyphenyl)-äthyldimethylammoniumbromid Zu einer Lösung von ioo g m-Dimethylaminophenol in iioo ccm Aceton werden 15o g Äthylbromid zugesetzt. In einer Stickstoffatmosphäre und in geschlossenem Gefäß wird die Lösung während io Stunden bei 8o° erwärmt. Es scheidet sich ein öliges Produkt ab, das bald kristallisiert. Das Produkt wird abfiltriert und in einem Gemisch von Äthanol und Äther umkristallisiert; die Kristalle bestehen aus (3-Oxyphenyl)-äthyldimethylammoniumbromid vom Schmelzpunkt 151 bis i52 (unter Zersetzung).The compounds of the formula (I) in which R is a methyl group, are preferably obtained in that m-dimethylaminophenol by means of a compound is quaternized, which enables the introduction of the ethyl group and an anion is such as B. an ethyl halide, diethyl sulfate, or ethyl p-toluenesulfate; those compounds in whose formula R is an ethyl group are on best obtained by quaternizing m-diethylaminophenol by means of a compound which is capable of introducing a methyl group and an anion, such as for example a methyl halide, dimethyl sulfate or p-toluenesulfonic acid methyl ester. Of the compounds obtainable by the process of the invention are those according to formula (I), in which X is a halogen, for example chlorine, bromine or iodine, most valuable as they are easily formed in crystallized form. example i (3-Oxyphenyl) ethyldimethylammonium bromide To a solution of 100 g of m-dimethylaminophenol 150 g of ethyl bromide in 100 cc of acetone are added. In a nitrogen atmosphere and in a closed vessel the solution is heated at 80 ° for 10 hours. It an oily product separates which soon crystallizes. The product is filtered off and recrystallized in a mixture of ethanol and ether; the crystals exist from (3-oxyphenyl) -äthyldimethylammoniumbromid from melting point 151 to i52 (under Decomposition).
Beispiel 2 (3-Oxyphenyl)-äthyldimethylammoniumjodid Eine Lösung von io g m-Dimethylaminophenol, 13 g Äthyljodid und 50 ccm Aceton wird 5 Stunden auf 5o° erwärmt. Nun wird Äther zur erkalteten Lösung zugefügt, worauf das (3-Oxyphenyl)-äthyldimethylammoniumjodid in Form eines bald kristallisierenden Öles abscheidet. Nach Umkristallisation aus Isopropanol schmilzt diese Verbindung bei 113 bis 115°.Example 2 (3-oxyphenyl) ethyldimethylammonium iodide A solution of 10 g of m-dimethylaminophenol, 13 g of ethyl iodide and 50 cc of acetone is heated to 50 ° for 5 hours. Ether is now added to the cooled solution, whereupon the (3-oxyphenyl) ethyldimethylammonium iodide separates out in the form of an oil which soon crystallizes. After recrystallization from isopropanol, this compound melts at 113 ° to 115 °.
Beispiel 3 (3-Oxyphenyl)-äthyldimethylammoniumchlorid Eine Lösung von 23 g Silbernitrat in 300 ccm Wasser wird mit einem leichten Überschuß einer io0/@gen Natriumhydroxydlösung versetzt. Das niedergeschlagene Silberoxyd wird mittels destilliertem Wasser frei von Silberionen gewaschen. Zur Suspension des Silberoxyds in 200 ccm Wasser wird eine Lösung von 25 g (3-Oxyphenyl)-äthyldimethylammoniumjodid in 300 ccm Wasser zugefügt. Der Niederschlag von Silberjodid wird abfiltriert und das Filtrat im Vakuum auf ein Volumen von etwa ioo ccm konzentriert. Die letzten Spuren Wasser werden durch Einfrieren und Trocknung des gefrorenen Produktes im Hochvakuum entfernt. Das (3-Oxyphenyl)-;ithyldimeth@,hininioniumhydroxyd wird in Form eines hygroskopischen, amorphen, festen Körpers erhalten. Eine Lösung von 5 g dieses Hydroxydes in etwa 200 ccm Wasser wird mittels verdünnter Salzsäure neutralisiert. Beim Eindampfen dieser Lösung zur Trockne im Vakuum kristallisiert das (3-Oxyphenyl)-äthyldimethylammoniumchlorid aus. Diese Verbindung wird aus Isopropanol umkristallisiert und schmilzt hierauf unter Zersetzung bei 162 bis 163y.Example 3 (3-Oxyphenyl) -äthyldimethylammoniumchlorid A solution of 23 g of silver nitrate in 300 ccm of water is mixed with a slight excess of a 10% sodium hydroxide solution. The precipitated silver oxide is washed free of silver ions using distilled water. A solution of 25 g of (3-oxyphenyl) ethyldimethylammonium iodide in 300 cc of water is added to the suspension of the silver oxide in 200 cc of water. The precipitate of silver iodide is filtered off and the filtrate is concentrated in vacuo to a volume of about 100 cc. The last traces of water are removed by freezing and drying the frozen product in a high vacuum. The (3-oxyphenyl) -; ithyldimeth @, hininioniumhydroxyd is obtained in the form of a hygroscopic, amorphous, solid body. A solution of 5 g of this hydroxide in about 200 cc of water is neutralized using dilute hydrochloric acid. When this solution is evaporated to dryness in vacuo, the (3-oxyphenyl) ethyldimethylammonium chloride crystallizes out. This compound is recrystallized from isopropanol and then melts at 162 to 163 y with decomposition.
Beispiel (3-Oxyphenyl)-äthyldimethylammoniump-toluolsulfonat In einem geschlossenen Gefäß wird eine Lösung von 15 g m-Dimethylaminophenol in 150 ccm Aceton 24 Stunden mit 25 g p-Toluolsulfosäureäthylester bei 8o° erwärmt. Das (3-Oxyphenyl)-äthyldimethylammonium-p-toluolsulfonat scheidet sich beim Versetzen der Acetonlösung mit Äther in Form eines zähflüssigen Öles ab. Dieses 01 wird in Wasser gelöst und die Lösung mittels Äther sorgfältig extrahiert. Beim Entfernen des Wassers durch Eindunsten im Vakuum wird die Verbindung als hygroskopische, zähflüssige Masse erhalten. Bei Verwendung von Diäthylsulfat an Stelle vonp-Toluolsulfosäureäthylesterwird (3-Oxyphenyl)-äthyldimethylammoniumäthylsulfat gewonnen.Example (3-Oxyphenyl) -äthyldimethylammoniump-toluenesulfonat In a closed vessel, a solution of 15 g of m-dimethylaminophenol in 150 cc of acetone is heated with 25 g of ethyl p-toluenesulfate at 80 ° for 24 hours. The (3-oxyphenyl) -äthyldimethylammonium-p-toluenesulfonate separates out when the acetone solution is mixed with ether in the form of a viscous oil. This oil is dissolved in water and the solution is carefully extracted using ether. When the water is removed by evaporation in a vacuum, the compound is retained as a hygroscopic, viscous mass. If diethyl sulfate is used instead of ethyl p-toluenesulfate, (3-oxyphenyl) ethyldimethylammonium ethyl sulfate is obtained.
Beispiel (3-Oxyphenyl)-diäthylmethylammoniumbromid In einem geschlossenen Gefäß wird eine Lösung von io g m-Diäthylaminophenol, 13 g Methylbromid in 50 ccm Aceton 4 Stunden bei 70° erwärmt. Es scheidet sich ein öliges Produkt ab, das beim Stehen kristallisiert. Dieses Produkt wird aus Isopropanol umkristallisiert, wobei (3-Oxyphenyl)-diäthylmethyl ammoniumbromid vom Schmelzpunkt 167 bis 16g° (unter Zersetzung) gewonnen wird.Example (3-oxyphenyl) diethylmethylammonium bromide A solution of 10 g of m-diethylaminophenol and 13 g of methyl bromide in 50 cc of acetone is heated at 70 ° for 4 hours in a closed vessel. An oily product separates out which crystallizes on standing. This product is recrystallized from isopropanol, (3-oxyphenyl) diethylmethyl ammonium bromide having a melting point of 167 to 16 ° (with decomposition) being obtained.
Beispiel 6 (3-Oxyphenyl)-diäthylmethylammoniump-toluolsulfonat In einem geschlossenen Gefäß und unter Stickstoff wird eine Lösung von 15 g m-Diäthylaminophenol, 17 g p-Toluolsulfosäuremethylester in 150 ccm Aceton 15 Stunden bei 8o° erwärmt. Das Aceton wird im Vakuum durch Destillation entfernt, der Rückstand in 250 ccm Wasser gelöst und die Lösung wird zur Entfernung von nichtumgesetztem Ausgangsmaterial mit Äther extrahiert. Beim Eindampfen der wässerigen Phase zur Trockne im Vakuum wird (3-Oxyphenyl)-diäthylmethylammonium-p-toluolsulfonat als hochviskoses 01 erhalten. Bei der Verwendung von Dimethylsulfat an Stelle von p-Toluolsulfosäuremethylester wird (3-Oxyphenyl)-diäthylmethylammoniummethylsulfat erhalten.Example 6 (3-Oxyphenyl) diethylmethylammonium p-toluenesulfonate In a closed vessel and under nitrogen, a solution of 15 g of m-diethylaminophenol and 17 g of methyl p-toluenesulfate in 150 cc of acetone is heated at 80 ° for 15 hours. The acetone is removed by distillation in vacuo, the residue is dissolved in 250 cc of water and the solution is extracted with ether to remove unreacted starting material. Evaporation of the aqueous phase to dryness in vacuum is obtained as a highly viscous 01 (3-oxyphenyl) -diäthylmethylammonium p-toluenesulfonate. When using dimethyl sulfate instead of p-toluenesulfonic acid methyl ester, (3-oxyphenyl) diethylmethylammonium methyl sulfate is obtained.
Claims (4)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US152998A US2647924A (en) | 1950-03-30 | 1950-03-30 | 3-hydroxyphenyl quaternary ammonium compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE837098C true DE837098C (en) | 1952-04-21 |
Family
ID=22545362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEH7251A Expired DE837098C (en) | 1950-03-30 | 1951-01-16 | Process for the preparation of quaternary 3-oxyphenylammonium compounds |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2647924A (en) |
| AT (1) | AT171418B (en) |
| CH (2) | CH296843A (en) |
| DE (1) | DE837098C (en) |
| DK (1) | DK76030C (en) |
| FR (1) | FR1033600A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3284297A (en) * | 1961-12-22 | 1966-11-08 | Thiokol Chemical Corp | 2-n-methylammoniumethylthiosulfuric acid and its use as a radioprotective agent |
| GB1325708A (en) * | 1970-05-28 | 1973-08-08 | Binns Ltd A J | Coat hook assembly |
| US4138435A (en) * | 1973-09-13 | 1979-02-06 | Lever Brothers Company | Detergent composition |
| US4687509A (en) * | 1986-05-19 | 1987-08-18 | The Dow Chemical Company | N,N,N-tributyl-(3-hydroxybenzyl)ammonium salts and a method for increasing yield of soybeans |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2208485A (en) * | 1937-04-24 | 1940-07-16 | Hoffmann La Roche | Process for the manufacture of disubstituted carbamic acid esters of phenols containing a basic substituent |
-
1950
- 1950-03-30 US US152998A patent/US2647924A/en not_active Expired - Lifetime
-
1951
- 1951-01-12 CH CH296843D patent/CH296843A/en unknown
- 1951-01-12 CH CH303167D patent/CH303167A/en unknown
- 1951-01-16 DE DEH7251A patent/DE837098C/en not_active Expired
- 1951-01-16 DK DK15851AA patent/DK76030C/en active
- 1951-01-19 AT AT171418D patent/AT171418B/en active
- 1951-01-20 FR FR1033600D patent/FR1033600A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1033600A (en) | 1953-07-13 |
| CH296843A (en) | 1954-02-28 |
| DK76030C (en) | 1953-06-29 |
| AT171418B (en) | 1952-05-26 |
| US2647924A (en) | 1953-08-04 |
| CH303167A (en) | 1954-11-15 |
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